Siege of Grosseto (1494)

The Siege of Grosseto (1494) was a military action of the Italian Wars that occurred when King Charles VIII of France's French royal army besieged the city-state of Grosseto in Tuscany. The French used their three artilllery batteries and one unit of organ guns to destroy the wooden walls of the city before overwhelming its defenders.

King Charles VIII had originally intended to conquer Grosseto after seizing Siena, as his plan was to bypass independent Italian city-states such as Piombino, Pisa, and Lucca in favor of advancing on Naples. He laid siege to Grosseto in mid-1494, but an assault on Siena by rebellious condottieri necessitated his return north to relieve the siege. After dealing with the mercenary threat, King Charles left a few troops billeted in Siena and proceeded to again lay siege to Grosseto. The city was defended by Pedro di Grosseto's 654 Grossetan troops, none of whom were a match for Charles' battle-hardened and numerically-superior army. The French used their heavy cannon to blast the wooden defenses of the city, and the defenders found themselves being pounded by cannonballs. The French pikemen - including hired mercenaries from Switzerland - would succeed in fighting the Grossetans until the last one was forced to surrender; only 45 Grossetan soldiers were captured alive, with the other 609 being slain. The French decided to punish Grosseto's civilians for their unwise resistance, massacring 527 people and looting 2,317 gulden from the city coffers.